1990 Fiscal Year Final Research Report Summary
Synthesis of Biologically Active Nitrogen Containing Aliphatic Compounds Using Nitroethanol as a Synthon.
| Project/Area Number |
01571140
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| Research Category |
Grant-in-Aid for General Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Research Field |
Chemical pharmacy
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| Research Institution | Faculty of Pharmaceutical Sciences, Chiba University |
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Principal Investigator |
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| Project Period (FY) |
1989 – 1990
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| Keywords | nitroethanol / nitroaldol reaction / ceramides / cerebroside B1a / chiral synthesis / pseudodistomins / (+)-erythro-N-lauroyldocosasphinga-4, 8-dienine / sialidase inhibitor / 095-acetamido-4-hydroxypipecolinic acid / 10absolute configuration |
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| Research Abstract |
A novel types of biologically active nitrogen containing compounds have been synthesized via the nitroaldol reaction using nitroethanol by our recently developed method as shown below.
1. Synthesis of Cerebroside B1a, 1a
Synthesis of four diastereoisomeric ceramides including the aglycone cerebroside B1a, 1a, was achieved, one of which was converted to the optically active 1a by glycosylation. Consequently, the absolute configuration of 1a was determined to be (2S,3R,4E,8Z,2'R)-1-0-(beta-D-glucopyranosyl)-N-(2'-hydr-hexadecanoyl)-4, 8-sphingadienine.
2. Synthesis of (+)-erythro-N-lauroyldocosasphinga-4, 8-dienine, 2.
The racemic 2 was synthesized by the simple method developed by the total synthesis of 1a. Optical resolution gave (+) and (-)-2. We also synthesized the optically active 2 by two different chiral synthesis.
3. Synthetic approaches to the pseudodistomins A (3a) and B (3b) novel antineoplastic piperidine alkaloids with calmodulin antagonistic activity from the Okinawan Tunicate Pseudodistoma Kanoko
We have established the synthesis of the piperidine ring which has the requisite three substitutents at the proper position by three different approaches.
4. Sialidase inhibitor, 5-acetamido-4-hydroxypipecolinic acid 4
The compound 4 was synthesized by analogous method used for the synthesis of 3.
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